Life, etc

Death of a humorist: The beautiful pessimism of David Rakoff

By Kevin Bloom 14 August 2012

Last week, a writer died in Manhattan who was to the virtues of pessimism what Norman Vincent Peale was to positive thinking: a founding father. In fact, David Rakoff probably demonstrated a truth about “doubt” better than any humorist had ever done before him: without it, there can be no irony. KEVIN BLOOM reflects on the passing of a profoundly sad and funny man.

In the opening sentence of the opening essay of David Rakoff’s 2010 collection Half Empty, the reader is introduced to a sensibility that she knows she is going to like. I don’t mean “any” reader, mind you, I mean the sort of reader who understands the real reason not to read EL James’s Fifty Shades of Grey: because it is an immoral book that robs life of its necessary sorrows and perpetuates the lie that redemption can be found in an egregiously rich and everlastingly tumescent man-god.

No, the Rakoff fan is more honest than that; she gets that erections eventually subside, that vast wealth is a chimera, and that Christian Grey is a psychotic and abusive nut-job. For her, the fairy tale promises of childhood have fomented into a robust and clear-eyed pragmatism, and irony—with its undercoat of sadness—has become a literary prerequisite. To wit, the following opening gambit: “We were so happy.”

Four words in, and not only has Rakoff suggested that happiness exists only in hindsight, but also that this axiom—if we have been battered enough by life to appreciate it—is morbidly funny. The third paragraph of his essay “The Bleak Shall Inherit” explains, on the perfect comedic beat, when it was exactly that we (as in the Royal We) were so happy:

“The millennium had turned. The planes had not fallen from the sky, the trains had not careened off the tracks. Neither had the heart monitors, prenatal incubators, nor the iron lungs reset themselves to some suicidal zero hour to self-destruct in a lethal kablooey of Y2K shrapnel, as feared. And most important, the ATMs continued to dispense money, and what money it was.”

Not funny? Then maybe you lost your shirt in the financial crisis, or, God forbid, suffer from the same terminal illness that finally claimed Rakoff’s life on Thursday, 9 August, at the age of 47, and have so far (and understandably) failed to find the humour in it. Because for the deeply mourned writer, humour in the face of the unfairness-of-it-all was indispensible, arguably the one thing that kept him going.

Born in Montreal in 1964, and reared in Toronto, Rakoff was diagnosed with Hodgkin’s lymphoma while in Japan at the age of 22. He returned to Canada for treatment, and when his disease went into remission—where it would remain for two decades—he moved to New York, landing a job in publishing. In 1998, he made the jump to a full-time writing career, thanks in large part to the mentorship and keen interest of the already famous humorist, David Sedaris.

In 2010 on Canadian national radio, Rakoff described himself as a “New York writer” who also happened to be a “Canadian writer,” a “mega Jewish writer,” a “gay writer'” and an “East Asian Studies major who has forgotten most of his Japanese” writer. More memorable, however, was his description of a pair of dotcom executives in the abovementioned essay from his Half Empty collection.

It was just after George “Dubya” Bush had won the US presidential race, and one of these hotshots had informed Rakoff, who’d been sent out to do an interview for a magazine, how, in the luminous media dawn brought on by the New Millennium, it was more important that you watched The Sopranos than who you voted for.

Wrote Rakoff: “They weren’t saying anything terribly incendiary. It’s not like they were proposing tattooing people who have HIV the way odious William F. Buckley did (I’m sorry, I mean brilliant and courtly, such manners, and what a vocabulary! Nazi …). But we had just been through an electoral experience that had been bruising, to say the least. Who one voted for had almost never seemed more important, and they were saying it all so blithely. I felt like a wife who has caught her tobacco-and-gin-scented husband smeared in lipstick, a pair of silk panties sticking out of his jacket pocket, home after an unexplained three-day absence, listening to his giggling, sloppily improbable, and casually delivered alibi and being expected to swallow it while chuckling along.”

Anyway, that was one of the (very many) humorous parts. As for the sorrow parts, Rakoff laid out in the essay his personal philosophy of “defensive pessimism”—in a nutshell: the mental stance of always expecting the worst so that you will never have to suffer the tortures of disappointment. The philosophy, which is actually more a technique for managing anxiety, was first laid out in the psychologist Julie Norem’s book The Positive Power of Negative Thinking, and Rakoff writes of discovering it as if it were an encounter fated by heaven itself (or, if not exactly heaven, then at least the floor in purgatory where they put short, gay, neurotic Jews who are bullied to within an inch of their lives at high school).

Naturally, at the core of defensive pessimism is the all-important ingredient of irony, an ingredient as lacking in the make-up of the so-called “dispositional pessimist” (the person who assumes that everything is going for a ball of shit, so why get out of bed?) as it is in the EL James fan. On the other hand, where the born optimist may be au fait with irony, he is only using it to stave off the possibility that things may, in fact, not turn out as planned—Norem calls this “ironic processing,” scientific jargon that would appear to distance the optimist somewhat from the innate ironist, who finds the world funny for the very reason that he approaches it from a position of doubt.

Which leads us to an interesting question: Is the strongest and most enduring humour therefore always a product of the mind and pen of the pessimist? By the end of “The Bleak Shall Inherit,” you’re pretty much convinced that it must be. Especially when, after debating with himself for pages over whether positive thinking and a sunny disposition has any intrinsic health benefits (apparently, there is real scientific data to suggest that it doesn’t) Rakoff hits you with this:

“The sunniest, most positive child in Malaysia labouring in a fucking sneaker factory can visualise all the good fortune he wants, but without concrete changes in international models of global trade, finance, and educational opportunities along with some very real temporal man-made policies, just for starters, guess where he’s going tomorrow morning? (A hint: it rhymes with schmucking sneaker factory).”

So David Rakoff, the beautiful pessimist, is no more; he died of the cancer that returned to claim him. No more will we read new lines as brilliant as his explanation of where he stands on that female songstress with the heroic nose: “On the Barbra [Streisand] spectrum—ranging from pure antipathy, like my friend Julie, who can only refer to her as ‘such a bitch!’, to the girls with whom I went to high school, for whom Ms. Streisand was the Jewish Steven Biko—I’m somewhere south of the middle.”

No more sublime takedowns (pun intended) like his impressions of the Concorde, when he sat aboard one of the aircraft’s last flights while researching a piece on conspicuous consumption: “At 42,000 feet and Mach 1.71 (1,110 m.p.h.), we are given some small canapés. Triple rounds of edible money: filet mignon topped with caviar, smoked salmon, foie gras and a gooseberry.”

No more the remarkable and peerless self-awareness, as in his description of why—aside from his tiny, unintimidating stature—people always seemed to want to confide in him: “I was there, but not there. In gypsy folklore, when one has a secret that can no longer be borne in silence, one digs a hole in the ground and speaks those terrible truths into it. I was that hole. But a hole with a difference. A hole who could arrange his features and posture into an expression simultaneously neutral and un-morbidly curious. A hole who knew enough, once confided in, not to be a malicious blabbermouth.”

And whatever Rakoff’s humour was, it was never malicious. He was too sad and world-weary for that; too intrinsically empathetic. In a universe where EL James novels are garnering 10,000-plus reader reviews on Amazon, where the soulless and the un-ironic and the belligerently optimistic insist on spreading their long-since-discredited positivity vibes, at least there was Rakoff: still as dubious about it all in his prose as he once was in life. DM

Read more:

  • “Remembering David Rakoff”—six classic Rakoff pieces from   

Photo: David Rakoff (Wikimedia Commons)



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